


Dicks, Dinner, and Diplomacy

by Koschei14



Category: Critical Role (Web Series)
Genre: Choking, Edgeplay, F/M, Magic, Nipple Piercings, Public Hand Jobs, Scratching, Sex Magic
Language: English
Status: Completed
Published: 2020-06-26
Updated: 2020-06-26
Packaged: 2021-03-03 20:41:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,014
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24921727
Author URL: https://archiveofourown.org/users/Koschei14/pseuds/Koschei14
Summary: Jester gets bored during a banquet, and Caleb makes use of his magic. Minor spoilers up to C2EP93.
Relationships: Jester Lavorre/Caleb Widogast
Kudos: 52





	Dicks, Dinner, and Diplomacy

Caleb tensed.  
As the bridge between the Empire and the Dynasty, the Nein found themselves in a precarious diplomatic position, where amongst courts built by and from the most powerful and perceptive members of both societies and tides of divination magic present on both sides, magic of which Caleb was upsettingly familiar with, it felt as if even thinking the wrong thoughts could land their entire found family into ruin. Despite their reputation as a chaotic bunch, Caleb believed that the Nein had the initiative to rise well above challenge, and through it maybe bring about a peace in Wildemount that the continent had not known for years. Seated at his right, Jester blew bubbles in her chocolate milk.  
At the marquis’ request in the early morning hours after the party, the Nein had been invited to a significantly more exclusive dinner, consisting of the highest echelon of people in Nicodranis and the Empire, the Marquis himself, and the Nein. Caleb suspected that particularly after their efforts during last night’s party to “talk to” Lord Thane, they were invited both to inspect the group as key players relevant to the peace summit, and as the morons-of-interest that the Nein had garnered a hard-earned reputation as wherever they passed through. Across from Caleb, Lord Robert Sharpe eyed daggers at Jester. Supposedly he spent nearly an hour and a half trapped on the balcony after the lock 'miraculously degraded.’ Sharpe claimed sabotage at the hands of the beloved heroes of the Empire and Dynasty, but without any legitimate evidence these claims were tragically discounted.  
They all sat at a long, ornate table of dark maroon, almost black wood, topped with a red tablecloth and the best of the Marquis’ fine dinner-ware. A long row of ivory candelabras, depicting various female forms propping up golden candle trays laid across the table’s length. The dining hall was remarkably wide and sparsely furnished, in a way that made the room feel colder and emptier the further from the table one looked. Caleb’s party occupied one whole side of the table, while the Marquis sat at the head on the opposite side far from him. Around them, servants scrambled to offer drinks, set plates and otherwise, and then with a wave, quickly vanished. The last remaining of the servants raised a hand, and each candle along the length of the table lit in unison. The lights around the large dining hall seemed to dim in order to assign extra significance to the table’s glow.  
Monsters, demons, pirates, and possesed friends, Caleb could handle with ease. But social interaction? The very thought churned in Caleb’s stomach. Thankfully, most of the conversation was going on at the other end of the table. Fjord had eschewed his glorious hat after the party, and Yasha her fine dress entirely, but the Nein maintained an unexpectedly professional tone, discussing goals in the peace effort and regaling the lords with only mildly embellished stories from the Nein’s antics thus far. Right of Jester, Beau cupped her face in her hand and gently massaged her temples, recovering from a “magic hangover,” and Jester herself looked… frankly, bored. Plot and politics just weren’t her scene, and gears were cranking in the blue tiefling’s head on just how to Traveler things up. Gods help whoever she chose to traumatize tonight.  
Caleb felt a narrow hand begin to gently slide up his thigh. What was she- Oh. Her hand found it’s prize, and took to gently massaging the length of it. Caleb’s eyes widened to dinner plates. Gods help him. He slipped a glance sideways, but Jester was staring straight across the table, an unmistakable smirk wide across her lips. 

“So, ummmmmmmmm, Mister Sharpe-”

“Erm, Lord Sharpe, if you please..”

“Oh, oh, yeah, of course, Looo-ooord Sharpe, I wanted to say we all are SO sorry about what happened to you last night! Getting stuck on that balcony? You must just have the WORST luck, rii-ight?” Jester’s voice had an especially affected tone to it, as intentionally tooth-gritting to Sharpe as it was to Caleb, albeit for starkly different reasons. The latter assessed the room in casually frantic glances, but with the nature of their seating and the tablecloth that hung low towards the floor, no one would be any the wiser to the fact that Jester had just wrapped her fingers around his quickly stiffening member. Lord, it had been a while, hadn’t it? Caleb drew in a sharp breath as he felt a hand tug at his belt. The effort wasn’t perfect, and she fumbled for a few moments, but she managed to loop her thumb under his belt and unlatch it. The buckle clinked against another part of itself, barely audible, and Caleb just about choked on his tongue.  
It’s not as if Caleb was about to stop her- this wasn’t the first time she did something like this. But, mein gott, here?? Caleb swallowed, hard, and scooted in closer under the table. Her hand made its way into his pants, and felt through his undergarments the length of what interested her. Despite his scrawny physique and general lack of experience with it, Caleb did have a very specific anatomical majesty most didn’t anticipate. She wrapped her hands around the thick base of his member, massaging it slowly with her thumb. Caleb sucked his lower lip to keep from making noise, occasionally exhaling hard through his nose. Ach, were her hands soft. 

“Hey.” A deep voice broke his dizzying haze, and Caleb practically bit through his lip. To his left, at the very end of the table, was Caduceus. Caleb had completely forgotten he was there. 

“You don’t look so good, buddy. Do you need to take a step outside, maybe?”

Caduceus was right, of course. Caleb was beet red, eyes laser-focused on the remaining half of the steak left on his plate in a death stare that didn’t break when he spoke. He hadn’t lifted his fork in ten minutes. “Oh, oh, noo. No. Just, uh, drank my wine too fast. You know me. Lightweight.” With a poor attempt at deception against Cad’s wise eyes, the firbolg glanced past him, at Jester, who was maintaining the same, torturously awkward conversation with Sharpe. She glanced over to him, and smirked twice as wide.  
.  
“Ah, right,” Caduceus said, calmly. “I’ll leave you two to it, then,” and went back to eating his salad.

Caleb looked down sheepishly, but Jester seemed to take his words as permission to hastendly began to stroke the length of his shaft. In truth, she was never very experienced in this sort of thing, but getting a reaction was so easy when Caleb was pent up. Not like she had been keeping track of him or anything, but so far as she was aware, Caleb wasn’t usually one to prioritize taking care of himself in that, or any other way. Lately, when he came, she tried to be involved in one way or another, and if that was the case, it had been a few weeks, at least. She took extra effort at times to run her thumb along the sensitive head of his penis, or sometimes when she felt he was getting too ahead of himself, limply hold his twitching cock in her hand for a moment, and watch him squirm out of the corner of her eye. Gradually, he began to gently gyrate in rhythm with her actions, using her hand as a tool for what had become the center of his attention at (or under) the table. Jester was more than willing to humor him, of course, but would sometimes ask him a question within her conversation and watch him stammer out a half-baked response, just to keep him behaved.  
Caleb was panting under his breath now, less subtly than he desired. Everyone had moved on to post-meal drinks, and he was barely cogent enough to let the servants take his half eaten meal as they came around. Under the table, he was reaching his limit. He wrapped his hand around Jester’s, and humped, more desperately against her petite fingers. She pulled her hand away. There was an audible THUD as Caleb absentmindedly stamped his boot down in frustration. The attention of the table turned to face him. 

“Ja, um, as I was saying, it is late, we should probably get a move on, you know- prepare for the voyage. Lots of sailing ahead of us. Yup.”

Everyone muttered in vague agreement. He shot an insulted glance at Jester. She smiled, shrugged, and casually sucked a glaze of pre off two of her fingers. Caleb scowled and struggled to wrangle his pants back up without drawing any more attention to himself.  
\---  
The rest of the Nein had decided to spend more time out on the town together, but Jester and Caleb chose to retire early back to the Ball Eater. Caleb had intended to follow Jester home, a particular intent on his mind, but upon rounding the corner, she was already gone. Jester ran ahead, and making her way back first, decided to change into something more comfortable- specifically, nothing at all. The rigors of adventuring had given her some serious biceps, but her body was otherwise lithe, with some plumpness gathered around her thighs and behind. Her breasts barely fit B-cups, and were each topped with a small, dark blue nipple, both pierced with a silver barbell. Her whole body was freckled.  
It wasn’t long before there was a knock at the door- Jester thought he was wise not to keep her waiting as she threw the creaky wooden door open.  
Caleb cast Hold Person.  
Jester’s muscles stiffened as she was paralyzed where she stood. Caleb turned to close the door behind him, and took the time to slowly pace around to her back, his head held high, and slid his hands slowly from the top of her hips to cup the underside of her breasts.

“Mein fraulein,” he whispered in her ear, “you will have to be punished for your behavior tonight.” His hands encompassed the whole of her breasts as he tugged her nipples between thumb and forefinger, and exhaled satisfaction. Every inch of her was lusciously, supernaturally smooth, and gave way just barely under his grasp. But he had to carry on with things, and had better ideas than burning all his slots on upping one spell. Rounding back to her front again, he rolled his thumb across her lip. She wore a glossy navy lipstick tonight, and he wanted its shade all over him. Caleb wrapped his hands around her shoulders, and forced her onto her knees. An aspect of the spell’s purpose resisted him, but her body gave way. The spell, the body, the very nature of reality’s weave was his to manipulate, and he would make it obey. He unfastened his belt, and flopped his erect penis against her cheek. Her eyes, fixed forward, focused on the tuft of orange hair at the base of his cock. Caleb slid a thumb into her mouth to force it open enough, and pressed the very tip of his penis between her plump lips. He raised his other hand, and snapped, releasing the spell.  
Jester’s eyes flicked up to look at him, and with free control of herself, a grin broke across her occupied lips. His hand traveled from her mouth to the back of her head, wrapping around a handful of hair, and pressed her firmer against his maleness, to which she obliged him. He was so grabby tonight, she thought. Took him long enough. Taking him into her mouth, she swirled her tongue around the head of his penis. Her hand traveled south, between her legs. Caleb fidgeted with her, balling up wads of hair and hooking his fingers around her horns, moving his hands incessantly and grinding gently both from his hips and his hands, as Jester maintained her suction around him. A long, drawn out moan escaped Caleb’s lips. The motion between them maintained a gentle pace, tender and desperate and wordless, and Jester took him a mite deeper with each stroke, wandering her hands up his thighs for leverage.  
All at once, Caleb impaled Jester’s throat on his cock, and held her there. Her fingers tensed and dug into the weave of his dress pants, and her eyes watered. When he allowed her off, a thick ribbon of spit joined the two of them, and they both panted for a while. Caleb’s cock twitched, damp and needy.

“We are not… remotely done yet.”  
\---  
Caleb began to shed his formal wear, and Jester ran her fingers up the sides of his chest, beneath his shirt. At once, an unseen force pushed her backwards, onto the bed, and she felt ephemeral arms wrap around her from her shoulders. Schmidt. Jester was initially unsure about the prospect of involving an invisible arcane butler of Zemnian descent into their love life, but one of the great advantages of Caleb’s magical acumen proved to be that he could have a threesome just about whenever he wanted. The wizard in question, now stripped nude, knelt, wrapping his own arms around Jester’s thighs, and ran his tongue along Jester’s lips. He lingered for a moment, and Jester felt his hot breath against her, while Schmidt’s hands made their way around to pinch her nipples. His hands felt different from Caleb’s, but the motion felt the same, and as Caleb’s tongue probed into her nethers, working circles around her clit, it felt as if she had two of him. It crossed her mind that there probably was a spell for that, too. Caleb’s lips wandered northward far too soon for her tastes, planting small kisses along the grooves of her hips, tickling smooches up her belly, on her solar plexus, a lingering kiss on each of her nipples, teasing the second one between his teeth, a peppering along her neck, her cheek, and then a full-bodied kiss on her lips. With his right hand, he brushed the hair out from her face, and stroked the lobe of her ear, but Schmidt maintained his proximity over Jester’s breasts and Caleb’s other hand groped up and down her back and behind, as his hips aligned with hers. The length of his cock dragged up the entrance of her vagina, and back again. Caleb had intended to take the same laborious time he had thus far, but Jester had greater initiative, and wrapped her legs around him, plunging him inside and inciting a synchronized gasp from them both. 

“You are… very poorly behaved, Jester.”

“You kn-ow, you haven’t done much about it so far...” Jester responded, wiggling playfully from beneath him. Her tail coiled its way around his upper thigh, while she reached her hands out and raked her long nails against his chest, leaving pinkish jagged trails behind them. Caleb groaned, tugging at her hair with one hand. His hips churned absently against hers.

“Jeee-eez Caleb, you’re really no good at this dom thing, maybe you sho-”

“Be quiet.”

She obliged, against her will. Suggestion. Caleb leant forward.

“I am tired of your misbehaving.”

Schmidt’s hands wrapped around her throat.  
Caleb pulled out almost completely, and slammed forward again. He wrapped his arms around the tiefling’s back, tugging his fingers through her hair as he began to pound her relentlessly. The ephemeral hands around her neck tightened, not with force to hurt, but which denied her circulation and made her thoughts fuzzy. Immediately, the sensations overtook her, and her body melted under his ministrations. Her back arched to take him further and her long nails gripped the bedsheets at her sides tight. All she wanted was him, and he couldn’t get enough of her. His hands tugged at her hair, her breasts, dragged a thumb across her cheek as he held her in a kiss, never once slowing the pace of his hips’ rhythm. For the first few moments, Jester was unnaturally silent, bound by the spell, but with a motion the enchantment lifted, and oh, did she moan. It wasn’t clear if anyone had come back to the ship, but Jester didn’t care. If they were on the Ball Eater, they heard her. The whole dock heard her. It didn’t matter. She raked her fingers across his back, and it drove Caleb deeper into a frenzy. He bit and sucked along her collarbone, up her neck. Lighter, purplish marks that would darken into hickies were left in his wake. Caleb’s eyes screwed shut, and his motions grew faster and erratic.  
Jester, too, reached her limit point, and gyrated her hips in rhythm opposite to his, her moans crescendoing to splitting volume, her hands raked a final time, firmly down his back, and her body spasmed in ecstasy. Caleb gave no respite, never ceasing his motions, and each panted heavily, entangled with one another.

“Please…,” Jester whispered, “I want all of it.”

That is exactly what Caleb gave to her. Thrusting roughly, deeply inside her, everything he held inside him spilled out. Jester could feel any resistance disappear inside her, she was wet and full, while Caleb never stopped thrusting through his orgasm. A noise, between a moan and groan escaped his lips, and he collapsed atop his partner shortly after, still deep inside, and planted kisses up and down her neck. Caleb’s cock twitched deep inside Jester, sending sparks out through her sensitive system, while cum drooled down her thighs dripping in thick beads against the sheets. They laid there for a moment, bodies intertwined, spent and unmoving, each cradling the other’s bare body. Caleb was the one to break the silence.

“Did you get that out of your system, Jester?”

“Hfff- if THAT’s the reaction I get, I should do it more often…”

“I am just saying,” he corrected, pertly, “because, I swear if there is a fancy dinner after we make peace between the nations, and you start a war-”

“Heyheyheyheyheyyyy-” she interruped, smooshing his cheeks under either hand so her eyes met with his. “It’d be worth it.”


End file.
